Family-friendly vacation rentals in Western Massachusetts

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Western Massachusetts family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.
Apartment in Townshend
4.93 out of 5 average rating, 240 reviews

Private Apt. on Farm, Hot Tub with views!

MathildeRating, 5 stars3 weeks ago
Amazing view, great and comfy Airbnb. The hot tub is such a nice plus with the incredible view over the mountains. It was so well equipped we had most of our meals in the Airbnb because the kitchen was so functional. I highly recommend this Airbnb!
Top guest favorite
A hot tub is positioned on a wooden deck, surrounded by lush greenery and trees. It offers expansive views of the natural landscape, with gentle hills visible in the distance under a soft, overcast sky.
Apartment in New Paltz
4.97 out of 5 average rating, 545 reviews

Relaxing Spa Retreat~Gorgeous View~Walk to Village

StephenRating, 5 stars2 weeks ago
Such a perfect location for a weekend in new paltz and the views from the patio/hot tub are absolutely spectacular. Ami was a great host!
Top guest favorite
A charming red farmhouse is set against a backdrop of rolling hills and blue skies. The property includes a separate red building nearby, surrounded by lush green grass and a landscaped stone garden featuring colorful flowers and greenery.
Home in Colrain
4.94 out of 5 average rating, 179 reviews

Secluded Farmhouse Retreat - stunning views

ColinRating, 5 stars2 weeks ago
We were four retired couples. Worldly travelers used to very comfortable surroundings. No TV was fine for this occasion. The farmhouse is designed with furniture comfortable for all, appointed in a farmhouse motif, of course, but the design aesthetic is of a quality respectful of its guests. "Good enough", never is. Obviously, the quality of consideration our Host has for the farmhouse presentation is treat your guest with respect and it will be reciprocated. One of the individuals commented, prior to even unpacking: "Perfect Place!" While it rained, we did not have the opportunity to enjoy the firepit, but some enjoyed the Hot Tub, as we all talked late into the night. This is located "close enough", 10 min drive to "civilization", to sites and shopping but it's really a more slightly secluded, private environment whereby a large family or, like us, distinct families can share comfortably, "come and go" separately together or stay together, together. We enjoyed ourselves.
Guest favorite
An 8-person hot tub bubbles gently under the night sky, surrounded by trees. A scenic trail, lined with colorful lights, winds through the woods leading toward a well-lit deck. The inviting ambiance is set for relaxation and exploration.
Bungalow in Easthampton
4.92 out of 5 average rating, 505 reviews

The Creation Station

ErinRating, 5 stars2 weeks ago
John went out of his way to ensure we had a great stay. It was a great place that accommodates many and the hot tub was relaxing after a long day of golf.
Superhost
A charming farmhouse is depicted, featuring a white exterior and a welcoming red front door. Windows provide natural light, and a wood pile is neatly stacked beside the entrance. Lush greenery and seasonal foliage surround the home, set against a clear blue sky.
Home in Northampton
4.88 out of 5 average rating, 638 reviews

The Farmhouse - Hot tub eclectic farmhouse 3 br

AngieRating, 5 stars1 month ago
This is our second time staying in The Farmhouse, and our 5th or 6th time booking with Ginny. This property is very relaxing, we brought our three dogs and they loved the backyard. The house was clean and organized. We enjoyed breakfast on the farmers porch. The hot tub was nice. It’s a quick drive to downtown NoHo, Florence and EastHampton. So much to do in this area. We highly recommend.
Superhost
A rustic living space features wooden beams and warm, ambient lighting. An antique stove serves as a focal point, surrounded by comfortable seating and a wooden table. Shelves filled with various items add character to the cozy atmosphere.
Cabin in Londonderry
4.81 out of 5 average rating, 477 reviews

Stunning Rustic Apple Barn - hot tub & sauna

ChristianRating, 5 stars1 week ago
We had a wonderful stay! It's such a beautiful and unusual cabin. It would be great for two couples as there are 2 equally great bedrooms that are quite separate, and a very nice sitting area around the amazing wood stove. (Which we didn't use because it's June and not necessary.) The hot tub was such a treat, and the bedroom with the boat was so cool. (OK, so maybe the bedrooms aren't quite equally great.) The kitchen is outstanding! We sat out on the porch a lot looking over the meadow, and I really liked that we were able to bring our dog. About the notes and instructions: they didn't bother us at all. There's a few non-intuitive features of the cabin, and it was useful to have clear guidance on those things. I want to make clear why I gave 4 stars for "cleanliness". I think they do an excellent job cleaning this cabin! But a rustic cabin like this is impossible to make "5-star clean". If you want or need that level of cleanliness, then "rustic" isn't for you! Go find a nice hotel.
Guest favorite
An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.
Home in Saugerties
5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

Zoe StarRating, 5 stars4 weeks ago
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***
Top guest favorite
An open-concept kitchen features a central island with bar seating for two, surrounded by wooden cabinetry and ample natural light from large windows. A dining area with a table for six is visible, complemented by wooden chairs and a cozy living space in the background, showcasing a comfortable setting.
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars3 months ago
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.

Family- and pet-friendly home rentals

Guest favorite
The entrance to the private suite features a wooden deck leading to a purple door. Large windows on either side allow natural light to illuminate the entryway. Surrounding greenery and a gravel pathway create a welcoming approach to the suite.
Home in Feeding Hills
4.89 out of 5 average rating, 977 reviews

Farm Fresh Feeding Hills

KaitlynRating, 5 stars1 week ago
A lovely place to stay. Beautiful view of the animals and mountains. Host was nice and accommodating.
Top guest favorite
Home in New Paltz
4.98 out of 5 average rating, 490 reviews

midcentury mod * POOL * walk out trail to mohonk

ArielRating, 5 stars2 weeks ago
This is a lovely house very close to New Paltz. We had a nice long weekend with the kids and loved spending time in the pool. Susan was a great host. No complaints!
Top guest favorite
A secluded apartment is surrounded by vibrant autumn foliage, with golden leaves adorning a tall tree in the foreground. The building features large windows that reflect the natural beauty of the landscape, enhancing its integration with the serene woods.
Apartment in Northampton
4.95 out of 5 average rating, 246 reviews

Cedar Wet Room w Soaking Tub

JazzRating, 5 stars3 days ago
Always a pleasure to stay here. Clean and quiet spot with everything you might need to make your stay pleasurable. I look forward to returning.
Top guest favorite
Barn in Guilford
4.99 out of 5 average rating, 126 reviews

The Carriage Barn

AristidesRating, 5 stars3 weeks ago
We really enjoyed our stay here. The place is incredible, you’ll have everything you’d need. Full of very thoughtful details. Very cozy, confortable and charming. The surroundings are beautiful and in a short drive you’d find anything you may need in Brattleboro. From dining to great coffee, groceries and more… I loved how simple and easy where the instructions for check-in and Out. Katherine was very friendly and responsive. Would definitely stay there again.
Guest favorite
A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars3 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Guest favorite
The spacious living and dining area features a fieldstone fireplace as a focal point. Exposed beams add character, while colorful hanging lamps brighten the space. A large wooden dining table is surrounded by sleek chairs, and cozy seating areas are arranged for relaxation.
Home in East Durham
4.93 out of 5 average rating, 248 reviews

Bluff House

ChuckRating, 5 stars4 weeks ago
We spent the weekend in the area and Tim’s place was fantastic. It’s loaded with charm, comfortable and very well appointed and stocked (right down to treats for the dog). The location is beautiful and the views are amazing. Can’t wait to return!
Superhost
A warm living area is featured, showcasing wooden walls and a vaulted ceiling. Comfortable seating is arranged around a coffee table with an assortment of plants. Large windows reveal a snowy landscape, while shelves display books and decorative items.
Cabin in Maplecrest
4.96 out of 5 average rating, 233 reviews

The Cabin - Ski House near Windham

CindyRating, 5 stars3 days ago
The cabin is beautiful and the perfect place to disconnect any time of year! It truly feels like a home away from home. We did run into a water issue during our stay, but Danielle took quick and thoughtful steps to resolve it and offered a very customer-centered solution. That really showed us how much she cares about her guests and takes her hosting responsibilities seriously. We had a wonderful time and definitely plan to be back soon!
Guest favorite
An open living area features a dining table surrounded by wooden chairs. A comfortable sofa sits near a coffee table, with an air conditioning unit and a television mounted on the wall. Wooden beams adorn the ceiling, contributing to a cozy atmosphere.
Cottage in Bernardston
4.88 out of 5 average rating, 324 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

JenniferRating, 5 stars1 week ago
This is the second time staying here and look forward to staying here again. Place is easy to get too and always very clean.

Family-friendly home rentals with a pool

Guest favorite
A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.
Home in Stormville
4.94 out of 5 average rating, 182 reviews

Private Hudson Valley Country Retreat

JackieRating, 5 stars2 weeks ago
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!
Top guest favorite
A child relaxes on a clear inflatable float in a sparkling swimming pool. Colorful bubbles and additional floats drift nearby, while sunlight reflects brightly on the water's surface. The pool's uniform depth is visible along the sides.
Apartment in Northampton
4.98 out of 5 average rating, 309 reviews

Sunny Inspirit Apartment in best downtown location

LauraRating, 5 stars3 weeks ago
very nice place! we slept very well! comfortable, quiet, relaxing! we would stay there again!
Guest favorite
A serene swimming pool is surrounded by well-maintained greenery, with lounge chairs placed along the deck. Large blue umbrellas provide shade, enhancing the outdoor space suitable for relaxation. A stone wall borders the area, adding a natural touch.
Home in Woodstock
4.94 out of 5 average rating, 239 reviews

Cedar Ridge: House or House+Apartment

AlissaRating, 5 stars1 week ago
We LOVED: 1) The location! The driveway is long & sand/gravel but you could drive it in a sedan fine. 2) The amenities! The pack n play was a HUGE lifesaver! 3) This location is mostly child friendly. 4) The view is phenomenal! When we woke up & opened the curtains for the first time, we were in awe! 5) The host was extremely helpful. The hot water went out once, but she was over in 5 minutes to fix it. Some feedback: 1) The windows in the ceiling in the master bed! They're HUGE and BRIGHT. 2) The bugs. Ants. Spiders. It was a struggle. NOW I WILL SAY - I brought this up to the host on day 3 and they were more than willing to come help how they could. The house is located in the middle of the forest, but it was a lot. If it weren't for an m&m left under the nightstand in the bedroom by a previous guest, it probably wouldn't have been so bad. 3) the coffee maker was pretty rough when we got there.. a simple over site by the crew. Overall, I would definitely consider this location again
Guest favorite
An above-ground swimming pool is featured in a spacious outdoor area, surrounded by a wooden deck adorned with colorful lounge furniture. Lush greenery provides a tranquil backdrop, enhancing the peaceful rural setting. A paved patio offers additional outdoor space for relaxation.
Guest suite in Brooklyn
4.93 out of 5 average rating, 190 reviews

Affordable In-Law Apartment in Brooklyn, CT

LyndaRating, 5 stars4 weeks ago
Thank you so much! Really enjoyed my time in brooklyn.
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 190 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

PaulRating, 5 stars6 days ago
We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.
Guest favorite
A scenic aerial view showcases an outdoor pool surrounded by greenery, with mountain vistas in the background. Lounge chairs line the poolside, inviting relaxation. The property features a blend of manicured gardens and natural landscaping, creating a peaceful environment.
Home in Woodstock
4.91 out of 5 average rating, 201 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars8 months ago
We loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼
Guest favorite
The pool area is framed by lush greenery, featuring a large in-ground pool with a slide. A colorful inflatable float is seen in the water. A shaded patio table with chairs provides a space for relaxation, alongside a sun umbrella that casts shade over the area.
Home in Williamstown
4.89 out of 5 average rating, 220 reviews

Hollywood Bungalow in the Berkshires #C0191633410

EveRating, 5 stars1 day ago
Diana and family were amazing super friendly, accommodating and checked in on use through out. We arrived later than expected but Diana waited for us and showed us around the property. We even got to see her dogs, meet her family, met the horse on the property behind and great conversations with Diana. She made us feel right at home. She prepped the pool for us, left us some good snacks and offered lots of recommendations. When you visit check out the theater set up, it’s pretty cool with insane sound system and clear video. Comfortable beds and all around beautiful property. If you visit in the summer it is a little warm on the second floor but we cooled off in the pool and just made sure to turn the fans on. It was the perfect birthday trip, relaxing, private and homey. My family and I are already looking forward to the next trip. Thank you to Diana for everything and hope we can meet again! 100% recommend.
Guest favorite
A serene pool area features a large in-ground pool surrounded by lush greenery. Several lounge chairs, including two green loungers and a round table with chairs, are situated on the patio. A bright red umbrella provides shaded seating, adding to the inviting outdoor space.
Guesthouse in Williamstown
4.93 out of 5 average rating, 241 reviews

Perfect Base for Your Berkshire Adventure

ChristinaRating, 5 stars1 week ago
Loved Mary's guesthouse! Great hosts who helped me with luggage. Beautiful surroundings with gardens and pool. Bed was super comfy and host provided coffee and fresh milk made my stay even better. Perfect place to stay for a visit to Williamstown!

Destinations to explore